In June 2018, Billy Jacobson met a guy on the dating app Grindr whom he recognized from the internet.

At the time, he’d been watching a lot of “RuPaul’s Drag Race,” and had come across a video of Evan Ross Katz, then a senior style editor at the media company Mic, interviewing the contestants Trixie Mattel and Katya Zamolodchikova.

“As Belinda Carlisle once sang, ‘Heaven Is a Place on Earth,’ and I am joined today by not one but two slices of heaven,” Mr. Katz quipped, introducing his blond-wigged guests, who immediately complimented his own hair, then dyed a bluish gray.

When Mr. Jacobson saw Mr. Katz in that video, he thought he was “kind of cute,” he said. “I could date him.”

Mr. Jacobson, now 30, “was on a bit of a mission to find a boyfriend,” he said. He had been trying to expand his social network — and dating pool — traveling to Cuba on a Jewish mission trip and volunteering with the LGBT Community Center in Manhattan.

“You were doing ‘The Secret,’” Mr. Katz, now 35, joked.